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Sodium Hydroxide → 4-(6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl)butanoic acid

HRID 2383321
ノート
印刷プレビュー

反応式

HRID 2383321 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:19]([CH3:43])=[C:20]4[C:25](=[CH:26][CH:27]=3)[CH:24]([CH2:28][CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[N:23]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:22][CH2:21]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].[OH-].[Na+]>C(O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[O:17][N:16]=[C:15]([C:18]3[C:19]([CH3:43])=[C:20]4[C:25](=[CH:26][CH:27]=3)[CH:24]([CH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:23]([C:36]([O:38][C:39]([CH3:40])([CH3:42])[CH3:41])=[O:37])[CH2:22][CH2:21]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 14798Sodium Hydroxide2 回HCID 595910951,1-Dimethylethyl 6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate

生成物 1

HCID 595910904-(6-(5-{3-Cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-2-{[(1,1-dimethylethyl)oxy]carbonyl}-5-methyl-1,2,3,4-tetrahydro-1-isoquinolinyl)butanoic acid収率 96.3%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

実験手順

To a solution of 1,1-dimethylethyl 6-(5-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-[4-(ethyloxy)-4-oxobutyl]-5-methyl-3,4-dihydro-2(1H)-isoquinolinecarboxylate (Preparation 29; 111 mg, 0.189 mmol) in ethanol (5 ml) was added 2M aqueous sodium hydroxide (0.189 ml, 0.377 mmol) and the resulting mixture was stirred at room temperature for 3 h. More 2M aqueous sodium hydroxide (2 equivalents) was added, and stirring was continued at room temperature for a further 3 h. Most of the solvent was removed and the residue partitioned between ethyl acetate and water. The aqueous layer was acidified with 2N aqueous hydrochloric acid, the layers separated, and the aqueous layer further extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated in vacuo to give the title compound (102 mg) as a white foam.

後処理

  1. stirringstirring
  2. waitwas continued at room temperature for a further 3 h
  3. customMost of the solvent was removed
  4. customthe residue partitioned between ethyl acetate and water
  5. customthe layers separated
  6. extractionthe aqueous layer further extracted with ethyl acetate
  7. dry with materialThe combined organic layers were dried over MgSO4
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-36ca5fff28fa42418334c77ed4623eac
出典データセット
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08263620B2

反応ノート

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